The proposed investigation explores major conceputal issues concerning mentoring and its contribution to stress resistance among high risk youth. Mentoring will be examined within the context of an intervention model that pairs pregnant adolescents with volunteer mentors from within the community. Young women will be randomly assigned to treatment (mentor) and control conditions (no mentor) conditions and group differences will be assessed during their pregnancy and following childbirth. In addition, the developmental, familial, and ecological antecedents and correlates of natural and assigned mentor relationships will be examined. Finally, a structural equations model will be used to test the relationships implied by a conceptual model of mentoring, including the direct and indirect effects of mentor relationships on problem behavior, distress, stress, and coping. The proposed longitudinal study will be conducted with a sample of 900 urban, predominantly African-American students attending an alternative public high school for pregnant students. Over the course of the five year project, each of the 450 students in the treatment condition (protegees) will be assigned to a trained mentor. Baseline and multiple follow-up assessments of both the students and mentors will be conducted and birth outcomes will be evaluated. In addition, the mentors and protegees will provide an ongoing evaluation of the quality and intensity of the relationships. Findings from this investigation will increase our understanding of mentoring relationships across a particularly stressful period and add to growing literature on resilience.